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United States Patent (19) 11) 4,339,589 Steglich Et Al

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United States Patent (19) 11) 4,339,589 Steglich Et Al United States Patent (19) 11) 4,339,589 Steglich et al. 45) Jul. 13, 1982 54 PREPARATION OF 4-SUBSTITUTED 52 U.S. C. .................................... 548/228; 548/352; OXAZOLIDIN-5-ONES 562/441; 562/442; 562/443; 562/444; 562/445; (75) Inventors: Wolfgang Steglich, Berlin; Rudolf 562/446,562/553; 562/567; 562/568; 562/571; Hurnaus; Peter Gruber, both of 562/575; 562/433 Biberach; Boerries Kuebel, Berlin, all 58) Field of Search......................................... 548/228 of Fed. Rep. of Germany (56) References Cited 73) Assignee: BASF Aktiengesellschaft, Fed. Rep. U.S. PATENT DOCUMENTS of Germany 3,676,453 7/1972 Pines et al........ ... 548/228 (21) Appl. No.: 175,593 4,264,771 4/1981 Stealich et al. ..................... 548/228 22 Filed: Aug. 5, 1980 Primary Examiner-David B. Springer Attorney, Agent, or Firm-Keil & Witherspoon Related U.S. Application Data 57 ABSTRACT 63 Continuation of Ser. No. 891,456, Mar. 29, 1978, Pat. Manufacture of 4-substituted oxazolinone-(5) com No. 4,264,771, which is a continuation of Ser. No. pounds, which are intermediates for substituted aminoa 484,068, Jul. 16, 1974, abandoned. cids, by alkylation of 2-substituted or 3,4-disubstituted (30) Foreign Application Priority Data oxazolinone-(5) compounds in an aprotic solvent in the Jul. 19, 1973 (DE) Fed. Rep. of Germany ....... 2336718 presence of a tertiary amine. 51) Int. Cl. ............................................ C07D 265/10 7 Claims, No Drawings 4,339,589 1. 2 zyl, diacetoxybenzyl, methylenedioxybenzyl and p PREPARATION OF 4-SUBSTITUTED chlorobenzyl. OXAZOLDIN-5-ONES Further possible substituents of the alkyl radicals are alkoxy, alkylthio, acylamino and carbethoxy radicals, This is a continuation of application Ser. No. 891,456, 5 such as methoxymethyl, S-methylthioethyl, y filed Mar. 29, 1978, now U.S. Pat. No. 4,264,771, which acetylaminopropyl, y-benzaminopropyl, 6 is a continuation of Ser. No. 484,068, filed July 16, 1974, acetylaminobutyl, 8-benzaminobutyl, carbethox now abandoned. ymethyl, carbethoxyethyl, 6-carbethoxymethyl and This invention relates to a process for the production g-carbethoxyethyl. , of 4-substituted oxazolinone-(5) compounds. 10 Examples of aryl R2 are phenyl, p-chlorophenyl, We have discovered a process for the manufacture of methoxyphenyl, dimethoxyphenyl, acetoxyphenyl and 4-substituted oxazolinone-(5) compounds, wherein 2 nitrophenyl. substituted oxazolinone-(5) compounds, which may Examples of cycloalkyl R2 are cyclopentyl, cyclo already have a substituent in the 4-position, are substi hexyl, cycloheptyl and cyclooctyl. tuted in the 4-position by reaction with an alkylating 15 The compounds of the formula I to be used as starting agent in an aprotic solvent in the presence of a tertiary materials can be obtained by conventional methods, for amine, and the resulting oxazolinone-(5) compound is example as described in the publication of H. E. Carter, optionally hydrolyzed to the aminoacid. "Organic Reactions'', Vol. III, page 198 (1949), or J. W. The starting materials are oxazolinone-(5) com Cornforth, "The Chemistry of Penicillin', edited by H. pounds of the general formula I 20 T. Clarke, J. R. Johnson and R. Robinson, Princeton University Press (1949), pages 730 et seq. H O I Alkylating agents are compounds by means of which alkyl or substituted alkyl radicals can be introduced into R?)-( compounds of the formula I. N - O 25 Examples of alkylating agents are therefore alkyl s halides, in particular alkyl bromides and alkyl iodides of Ri 1 to 10 carbon atoms, such as methyl, ethyl, propyl, butyl, and isobutyl bromides and iodides and 2-ethyl in which R1 is hydrogen, an unsubstituted or substituted hexyl bromide. The alkyl halides can contain double aromatic radical, straight-chain or branched-chain un 30 bonds and triple bonds. Allyl halides, such as allyl bro substituted or substituted alkyl of 1 to 20, preferably 1 to mide or prenyl chloride and propargyl halides, such as 10, carbon atoms, or a cycloaliphatic radical of 5 to 8 propargyl bromide or geranyl bromide, are preferred. ring members. In turn, the alkyl radicals can carry substituents and The preferred aromatic radical R1 is phenyl which accordingly the following can be used as alkylating can be substituted, for example by halogen, nitro, alk 35 agents: benzyl halides, for example benzyl chloride, oxy or lower alkyl, especially methyl or ethyl. benzyl bromide, nitrobenzyl chloride, dimethoxybenzyl Examples of substituted phenyl are chlorophenyl, chloride, p-chlorobenzyl bromide, methoxybenzyl bromophenyl, nitrophenyl, methoxyphenyl, dimethoxy chloride, 3,4-methylenedioxybenzyl chloride, acetoxy phenyl, tolyl and ethylphenyl. benzyl chloride, p-methylbenzyl chloride, 2,4-dimethyl Examples of suitable alkyl R1 are methyl, ethyl, pro benzyl chloride, 3,4-dimethylbenzyl chloride, trityl pyl, i-propyl-butyl, i-butyl, sec.-butyl, tert.-butyl, n-pen chloride or trityl fluoborate, halomethyl ketones, such. tyl, heptyl, octyl, decyl and dodecyl. as phenacyl bromide and chloroacetone, chloroacetic Examples of substituents of the alkyl radicals are acid or chloroacetic acid esters, for example ethyl chlo amino groups which carry an acyl radical as a substitu roacetate. ent of the nitrogen, such as 1-benzamino-isobutyl, 1 45 Tropylium perchlorate is a further example of a possi benzamino-2-phenyl-ethyl, benzaminomethyl, 1-ben ble alkylating agent. Zamino-ethyl and the corresponding acetamino radicals. As a rule, the reaction of a starting material with the Further substituents of the alkyl radicals are ester alkylating agent is carried out with equimolar amounts groups, nitrile and aryl radicals, especially phenyl radi in an anhydrous aprotic solvent in the presence of a cals, such as benzyl or 3-phenyl-ethyl. 50 tertiary amine as the base. However, one of the com Examples of cycloaliphatic radicals are cyclopentyl, pounds to be reacted can also be used in excess. cyclohexyl and cycloheptyl. Examples of suitable solvents to use are chlorinated The preferred starting compounds are 2-phenyl aliphatic hydrocarbons, such as methylene chloride or oxazolinone-(5) compounds which already have a sub chloroform, aromatic hydrocarbons, such as benzene or stituent in the 4-position, so that 4,4-disubstituted ox 55 toluene, amides of lower aliphatic carboxylic acids, in azolinone compounds are produced by the process of particular dimethylformamide or hexamethylphos the invention. phoric acid triamide, or dimethylsulfoxide, or mixtures R2 is hydrogen, straight-chain or branched-chain of the said solvents. alkyl of 1 to 20 carbon atoms, which can be substituted, . A solvent of low polarity, such as benzene, methy unsubstituted or substituted aryl or cycloalkyl of 5 to 8 lene chloride or tetrahydrofuran, is appropriate for very ring members. reactive alkylating agents, such as, for example, trityl Individual examples of R2 are: as alkyl-methyl, chloride, tropylium perchlorate or phenacyl chloride, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl, pen for alkylation with alkyl halides, the use of dipolar tyl, heptyl, octyl, decyl, dodecyl and pentadecyl; as aprotic solvents, such as dimethylformamide, dimethyl substituted alkyl-in particular, alkyl substituted by 65 sulfoxide or hexamethylphosphoric acid triamide is phenyl which may be additionally substituted in the preferred. aromatic ring, such as benzyl, 9-phenylethyl, 3-phenyl Examples of suitable tertiary amines to use, which are propyl, methoxybenzyl, dimethoxybenzyl, acetoxyben in general employed in excess, are triethylamine, ethyl 4,339,589 3 4. diisopropylamine, so-called Hinig's bases (Hinig and Kiessel, Chem. Ber, 91, 308 (1958)), N,N-dimethyl CH3 CH-COCH3 cyclohexylamine, pyridine or picolines. Ethyldiiso N CH-C-COOH propylamine has proved a particularly suitable base. / In general, the reactions are carried out at tempera CH3 NH2 tures from 0° C. to room temperature or at elevated temperatures, suitably up to 100° C. At times it can also Further examples of aminoacids are a-phenacetyl glutamic acid, O-ethyl-lysine, a-propyl-ornithine and be appropriate to carry out the reaction at temperatures a-(o-nitrobenzyl)-ornithine. below 0°C., for example at -10° C. or below. 10 In some cases, for example when using benzyl chlo EXAMPLE 1 ride or ethyl chloroacetate as alkylating agents, the 4-allyl-2-phenyl-4-benzyl-oxazolinone-(5) addition of potassium iodide assists the alkylation. Working up the resulting 4-substituted oxazolinone 10 g (40 millinoles) of 2-phenyl-4-benzyl-oxazoli 15 none-(5) and 4.9 g (40 millimoles) of allyl bromide in 50 compounds presents no difficulties and is carried out by ml of absolute dimethylformamide are stirred with 6.75 conventional methods, for example by adding water g (51.5 millimoles) of ethyldiisopropylamine for 4 days and extracting by shaking with a water-insoluble or at room temperature. 200 ml of water are then added ganic solvent. and the mixture is extracted with five times 30 ml of It is surprising that under the reaction conditions 20 methylene chloride. The combined extracts are ex according to the invention the 4-substituted and 4,4- tracted by shaking with 0.5 N hydrochloric acid and disubstituted oxazolinone derivatives can be manufac with water and then dried over magnesium sulfate, and tured from optionally 2-substituted oxazolinone-(5) the solvent is evaporated off under reduced pressure. compounds without difficulties and in good to very 4-allyl-2-phenyl-4-benzyl-oxazolinone-(5) remains as a good yields, whilst from the known state of the
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